Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins

Mei Huey Lin; Yi Syuan Li; Chung Kai Kuo; Chung Hao Chen; Yen Chih Huang; Kung Yu Liang; Yu Chun Chen; Chang Hsien Tsai; Tsung Hsun Chuang

doi:10.1021/acs.joc.5b00072

Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins

Mei Huey Lin, Yi Syuan Li, Chung Kai Kuo, Chung Hao Chen, Yen Chih Huang, Kung Yu Liang, Yu Chun Chen, Chang Hsien Tsai, Tsung Hsun Chuang

Department of Chemistry

Research output: Contribution to journal › Article

5 Citations (Scopus)

Abstract

A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr₃-mediated S_N2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels-Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.

Original language	English
Pages (from-to)	2462-2466
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	80
Issue number	4
DOIs	https://doi.org/10.1021/acs.joc.5b00072
Publication status	Published - 2015 Feb 20

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All Science Journal Classification (ASJC) codes

Organic Chemistry

Cite this

Lin, M. H., Li, Y. S., Kuo, C. K., Chen, C. H., Huang, Y. C., Liang, K. Y., Chen, Y. C., Tsai, C. H., & Chuang, T. H. (2015). Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins. Journal of Organic Chemistry, 80(4), 2462-2466. https://doi.org/10.1021/acs.joc.5b00072

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abstract = "A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated SN2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels-Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.",

author = "Lin, {Mei Huey} and Li, {Yi Syuan} and Kuo, {Chung Kai} and Chen, {Chung Hao} and Huang, {Yen Chih} and Liang, {Kung Yu} and Chen, {Yu Chun} and Tsai, {Chang Hsien} and Chuang, {Tsung Hsun}",

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Synthesis of hexahydro-1 H-isoindole derivatives from arylacyl bromides via homoallenic bromohydrins. / Lin, Mei Huey; Li, Yi Syuan; Kuo, Chung Kai; Chen, Chung Hao; Huang, Yen Chih; Liang, Kung Yu; Chen, Yu Chun; Tsai, Chang Hsien; Chuang, Tsung Hsun.

In: Journal of Organic Chemistry, Vol. 80, No. 4, 20.02.2015, p. 2462-2466.

Research output: Contribution to journal › Article

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AU - Lin, Mei Huey

AU - Li, Yi Syuan

AU - Kuo, Chung Kai

AU - Chen, Chung Hao

AU - Huang, Yen Chih

AU - Liang, Kung Yu

AU - Chen, Yu Chun

AU - Tsai, Chang Hsien

AU - Chuang, Tsung Hsun

PY - 2015/2/20

Y1 - 2015/2/20

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AB - A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated SN2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels-Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.

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10.1021/acs.joc.5b00072